"Shrewd as serpents"; what does that really mean?

"Shrewd as serpents"; what does that really mean?

As Yeshua gave His disciples directives for their mission of spreading the gospel message to the Jewish towns and villages of the Galilee, He warned His disciples that not everyone would receive their message. They should expect some rejection, and when it happened, they should leave that home or village, shaking the dust from their feet as they left.
Those warnings about future rejection led to a series of predictions about a coming time of persecution. Matthew 10:16 begins with the exclamation, “Behold!” signifying a break with the earlier instructions.
Behold, I send you out as sheep in the midst of wolves; so be shrewd as serpents and innocent as doves. (Matthew 10:16)

At this point, the discourse begins to address broadly the coming days of persecution and tribulation that the disciples could anticipate. The Master compared the disciples to “sheep among wolves.” The simile also appears in rabbinic literature where the midrash compares Israel to a lone sheep surrounded by seventy wolves, i.e., the seventy gentile nations:
How great is the sheep that stands among seventy wolves! How great is the shepherd who rescues and guards it, and who thwarts them from harming it. (Midrash Tanchuma)

Yeshua sent His disciples out as “sheep among wolves,” meaning that they could expect vicious treatment at their hands of men. Therefore, He advised the disciples to be “wise as serpents” when dealing with the wolves, that is to say, they were to be shrewd and cunning.
 
His words subtly allude to Genesis 3:1, “Now the serpent was more crafty than any beast of the field which the LORD God had made.” He did not tell His disciples to behave as serpents. He did not grant them permission to perpetrate fraud. They were to be “shrewd as serpents” by thinking ahead, anticipating danger, and avoiding persecution and arrest whenever possible, but they were not to conduct themselves as serpents. Instead, they were to maintain the kingdom principles and conduct themselves “innocent as doves,” prepared to suffer when necessary.

Yeshua probably did not coin the phrase “be as shrewd as serpents and innocent as doves.” Instead, the pairing seems to have been a proverbial idiom meaning, “Be cautious and use common sense to your best advantage, but don’t compromise moral values.” The same pairing of similes appears in rabbinic literature:
The Holy Ones says, “With Me they are innocent like doves, but with the nations they are cunning like serpents.” (Song of Songs Rabbah2:34)

Disciples of Yeshua should never seek out persecution or martyrdom. We should exercise prudence and caution, doing our best to live at peace with all men, in as much as it depends upon us. At the same time, we must not be willing to compromise our mission or our principles, even when under the threat of persecution.
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